[MF] Breaking out of the friend zone and popping my cherry all in one night

This true story takes place in the mid 1980’s in a northern English market town. It is my first post so please let me know what your thoughts are.

First off about me, average geeky 19 yr old teenager tall with average looks and an average sized packet; Mr average all round. Her, tall brunette, same age, on the chubby side but sexy as hell with big tits, we’ll call her Jen.

We met at college and had known one another for 3 or 4 months. Because we lived in the same suburb we would often catch the same bus together. I would always make sure that i walked her home before heading to my house.

As I say I was a typical geeky teen and more than a little nervous, shy and socially awkward around girls. As much as I wanted to, I couldn’t bring myself to try it on with her, fear of being rejected was probably high on the list.

Thursday, Friday and Saturday nights were always huge party nights and going downtown to get hammered was the normal routine for most college students.

This one Friday I arranged to meet a few buddies in Spires after college to start the usual drinking games. Spires was a typical town center pub / bar. Previously it had been a spit and sawdust establishment called the Painted Wagon, but then it was updated with a glitzy bar and neon lights to try and appeal to the younger crowd. I guess it worked because this was where most college kids started out on Friday nights

Well this particular Friday evening I was the first one to arrive, so I bought a pint and went to find a quiet corner (difficult in Spires). As I turned around I felt this arm go around my waist and Jen is standing there with some of her friends, “ey up” she says “are you alone” Not really knowing what to do and feeling somewhat nervous being around a group of girls on my own, I kinda mumbled that I was but was waiting for some friends.

Jen offered that I could tag along with them, if I wanted to. After buying all the girls a drink we went and found a corner table. There wasn’t much space so Jen sat on my knee. A few minutes later a couple of my buddies walked in and saw me sitting in the corner with a group of girls, let’s just say my reputation, albeit undeserved, was sealed. After the usual cat calling and piss taking they decided to leave, so here I was again nervous as fuck all alone with half a dozen girls. Can’t remember too much about the evening since it was 30 years ago and the alcohol was flowing. Suffice to say we left Spires and headed off to another couple of popular bars and pubs (Golden Fleece and The Market) Followed by Adam and Eves nightclub.

Once we hit the nightclub the girls all kinda went their own way and I propped up the bar. I was never much of a dancer probably down to me being socially awkward and having two left feet but never the less Jen dragged me on the dance floor for a couple of the slow ones.

2 am rolled around and if was kicking out time. Rather than cough for a taxi, Jen and I decided, in our semi drunken state to walk home. Newbold was probably a good 4 miles from the club, but we figured we could be home by 4ish. She told me i could crash on the couch at her mums house if I wanted.

As we walked she linked arms with me, a little while later on I put my arm around her to try and warm he up. About half way back she starts fidgeting and then decides to tell me she needs to pee. At this point we are on a main road and while not busy she point blank stated that she was not going to drop and squat there in public, she would simply have to hold it. At 3 am the traffic was negligible but her reason for holding was she did not want me to see or watch, fearing that I would try something on. A little while later she bent half double grabbed hold of me and squeezed my hand. After some deep breathing she stood up and we carried on walking.

By now even though I was concerned for her situation my dick was rock hard and tenting in my trousers. 10 mins later she leans up against a brick gate post half squats and then I hear her quietly sobbing, it was obvious what was happening but it was dark and I couldn’t see much, however my dick was ready to explode. Not sure what to do or say I gingerly put one hand on her back in between her shoulder blades and started rubbing while whispering In her ear not to worry and it would be alright.

After a short while she stood up still crying and asked me not to tell anyone, I gave her a gentle hug and kissed her on the forehead, how it happened I don’t know but it didn’t take long and our lips locked, wow what a night. She must have noticed the trouser tent because the next thing I feel is her hand rubbing my dick through my trousers. It was not many strokes before I blew my load right there in my pants. We both started laughing, me out of embarrassment. She said something along the lines that we both had wet underwear now and we both had a secret.

It took probably another hour before we got back to her house. When we walked in it was possible to see her jeans were still absolutely soaked, sometime later she told me that she peed them again before we arrived home. Her mother was waiting up for her and made her remove and empty her boots on the front step, before going upstairs.

Unbeknown to me her parents were very liberal and mum simply said well it’s very late and you two better get to bed. Jen grabbed my hand and dragged me upstairs.

We got in the bedroom Jen removed her jeans and then went to the bathroom. I laid on the bed and must have dozed off. The next thing I remember is Jen on all fours in a bath robe on top of me kissing me furiously. Returning the passion I slipped my hand around her waist but she sat up and started to unbuckle my belt and remove my trousers. As she did this her bath robe fell open revealing her beautiful 40 DD breasts. I couldn’t help but grab them and squeeze, sitting up and sucking madly on her saucer sized nipples. It didn’t take long and I worked one hand down between her legs touching and feeling her pussy for the very first time. I was still a virgin but had had a couple of girlfriends in the past who had let me have a good feel. Damn her pussy was dripping wet and as I inserted a couple of fingers she let out a moan and mumbled something like oh god under her breath. It didn’t take long before she had straddled me and I popped my cherry. The rest of the night or what was left of it was spent exploring and experimenting, I for one finally had an opportunity to try out some of the things I had only read about in porno mags, her lust was unbelievable and there was nothing off limits. I guess having witnessed her wet herself and being ok with it she figured that I was pretty much un-shockable and she could try anything. As for me I was game for anything.

We dated for about 6 months and then drifted apart but every now and then over the next couple of years we would hook up for a lust and fetish filled evening or weekend. If i get some good responses maybe I will continue to tell a few more of our stories.

Source: reddit.com/r/gonewildstories/comments/5x3r21/mf_breaking_out_of_the_friend_zone_and_popping_my